Solid-phase SNAr macrocyclizations to give turn- extended-turn peptidomimetics Academic Article

abstract

• Solid-phase supported SNAr macrocyclization reactions were investigated to test the viability of preparing libraries of -turn mimics. An optimized set of conditions for this type of transformation was developed for various amino acid derived nucleophiles and ring sizes. The reaction conditions were optimized for the ideal resin types, resin loadings, bases, and cyclization time for the macrocyclization reactions. Finally, these conditions were applied in a series of model syntheses in which the products were isolated and purified. Access to this type of peptidomimetic on the solid phase lays foundations for the syntheses of libraries designed for targets involving protein - protein interactions.

authors

• Burgess, Kevin

published proceedings

• CHEMISTRY-A EUROPEAN JOURNAL

altmetric score

• 9

author list (cited authors)

• Feng, Y. B., & Burgess, K.

citation count

• 40

complete list of authors

• Feng, YB||Burgess, K

publication date

• November 1999

publisher

• Wiley  Publisher

keywords

• Beta-turn
• Macrocyclizations
• Nucleophilic Aromatic Substitutions
• Peptidomimetics
• Solid-phase Synthesis

Digital Object Identifier (DOI)

• 10.1002/(SICI)1521-3765(19991105)5:11<3261::AID-CHEM3261>3.0.CO;2-H

start page

• 3261

end page

• 3272

volume

• 5

issue

• 11

URL

• http://dx.doi.org/10.1002/(sici)1521-3765(19991105)5:11%3C3261::aid-chem3261%3E3.0.co;2-h